Akinator

[Assertn]

Yeah. My friend from high school doesn't use a sentient weapon.

[Buffalobiian]

GOT:

Kenichi (History's Strongest Disciple)
Fai (Tsubasa Chronicles)
L (Death Note)
Ai (Mahou Shoujo Ai) -> didn't know it was into hentai as well
Yuuhi Katagiri (Akaneiro_ni_Somaru_Saka)
Ali (Gundam 00)
Kogarashi (Maid Guy)
Mewtwo (pokemon)
Kanou Kyosuke (Hungry Heart: Wild Striker)
Yin (Darker than Black)
Silvia De Alisia (Sousei no Aquarion)
Grace O'Conner (Macross Frontier ) -> with great difficulty, cycling through C.C., Tieria Erde, and "Does your character have small breasts?" 0_o

Alastor (Shakugan no Shana)
John Woo

MISSED:
Gunther (Kyou Kara Maou)
Himuro Izumi (Princess 9)
Bocca Seranade (Melody of Oblivion)
Briareos (Appleseed)
Richardo (El Cazador de la Bruja)

[Board of Command]

GOT:

Ai (Mahou Shoujo Ai) -> didn't know it was into hentai as well

I tried Ai and it didn't get it.

[Buffalobiian]

I tried Ai and it didn't get it.

The first time it got it within 20 questions. This second time took a bit longer, asking things about R&B and stuff....but it still got it by the 40th question. Apparently it's been only asked 200 something times, so it's not that common. Still, it's built up quite the question database already:

Is your character a female? Yes Yes
Is your character a singer, or does he work with a singer (as a songwriter, producer, musician...)? No No
Does your character personally know you? No No
Is your character American ? No No
Is your character real? No No
Does your character go to school? Yes Yes
Does your character have magical powers? Yes Yes
Does your character have long hair? No No
Does your character have a brother or sister? No No
Does your character like to read books? No No
Is your character the boss of a team? No Probably
Is your character from a video game? No Yes
Is your character black-haired? Yes Yes
Does your character fight with a sword? No No
Is your character a R'n'B singer? No ?
Can your character fly? No No
Does your character fight? Yes Yes
Is your character less than 15 years old? No No
Is your character from a novel? No No
Is your character English speaking? No ?
Has your character killed humans? No Probably
Does your character use magic? Yes Yes
Does your character fight against monsters? Yes Yes
Is your character linked with the color red? No No
Does your character wear a hat (cap, crown,...)? No No
Does your character have a sword? No Probably
Does your character have brown hair? No No
Is your character short-haired? Yes Yes
Does your character live with his mother? No No
Is your character in love with a man? Yes Probably
Is your character a junior high-school student? Don't know No
Is your character a ninja? No No
Has your character killed anyone? Yes Yes
Does your character have a great artistic skill? No No
Does your character have a older brother? No No
Is your character a girl? Yes Yes
Does your character put some accessories in his hair? Yes Yes
Is your character the eldest of the group? No ?
Is your character from a TV series? Don't know No
Is your character less than 18 years old? Yes Probably not

By far the least asked characters I've come across were Silvia De Alisia (Sousei no Aquarion) and Kyosuke from Wild Striker. They only had 7 asks before mine.

[rockmanj]

got: Kunckles, Malcolm X, Kara "Starbuck: Thrace

missed: my girlfriend (said "my mistress), and Tech N9ne.